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Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles

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Chemistry of Heterocyclic Compounds Aims and scope

The heterocyclization of 2-acetyl-3-indolylacetic acid hydrazones and its amides, in contrast to similar derivatives of phenylacetic acid, does not lead to 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino-[4,5-b]indoles but rather to 2-aminoindolo[2,3-c]pyridin-3(2H)-one or azines of 2-acetyl-3-indolyl-acetic acid. 2,3-Dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles were obtained by the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and of methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate.

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Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 83114, Donetsk, Ukraine

    V. S. Tolkunov, A. B. Eresko, A. I. Khizhan & S. V. Tolkunov

  2. STC Institute for Single Crystals, National Academy of Sciences of Ukraine, 61001, Kharkiv, Ukraine

    O. V. Shishkin & G. V. Palamarchuk

Authors
  1. V. S. Tolkunov
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  2. A. B. Eresko
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  3. A. I. Khizhan
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  4. O. V. Shishkin
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  5. G. V. Palamarchuk
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  6. S. V. Tolkunov
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Correspondence to V. S. Tolkunov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 907–917, June, 2009.

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Tolkunov, V.S., Eresko, A.B., Khizhan, A.I. et al. Heterocyclization of 2-acyl-3-indolylacetic acids using hydrazine. Synthesis of 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles. Chem Heterocycl Comp 45, 726–734 (2009). https://doi.org/10.1007/s10593-009-0322-7

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  • DOI: https://doi.org/10.1007/s10593-009-0322-7

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